When your boss Is crying, but you’re the one being laid off

If you had told Ryan Caldbeck, in his first job, that he would one day be crying to a room full of his employees, he might have simply told you – with the bluster characteristic of any corporate striver – that you were wrong.

But somewhere in between tumultuous markets and shifting national conversations on mental health, Caldbeck’s perspective changed. In 2016, he laid off roughly 15% of his 45-person team at financial technology company CircleUp, and broke down in tears. Now, he said, he shares his feelings with colleagues more openly. He also sometimes wrestles to find the line between buttoned-up executive reticence and oversharing.

“There was a time when I went into work, and in a meeting we were going around the room saying ‘how was your weekend,’ and I said, ‘Oh, I got in a difficult fight with my wife,’ ” said Caldbeck, 43, who was previously CircleUp’s CEO. “Everyone’s mouth dropped. I realized I went too far. That wasn’t appropriate. That’s not how to show vulnerability at work.”

CEOs have long studied how to deliver good news and bad news. They’ve trained themselves to pitch big ideas and shoot down middling ones. Now they have a new skill to learn: the art of being vulnerable. Emotional intelligence has landed atop the lists of bestselling management guides, like “Dare to Lead,” by Brené Brown, whose books on vulnerability have sold well more than 1 million copies. At the Stanford Graduate School of Business, the most popular elective course, for years, has been Interpersonal Dynamics, more commonly referred to as “Touchy Feely.”

“People in business are socialized to leave their feelings in the parking lot,” said Carole Robin, co-author of “Connect,” who used to teach “Touchy Feely.” “There’s a generation of leaders now – the ones that might be the really up-and-coming leaders of the future – who have discovered that actually it’s almost impossible to really inspire people in the absence of feelings.”

So, as companies navigate a challenging economic moment, executives are racing to let their employees know that they’re not just empty suits. They’re humans, with emotions, which they’re sharing on Twitter, in memoirs and in all-staff meetings. But their employees aren’t always benefiting from the results of all that sharing. And, in some cases, they’re feeling pressured to respond to their bosses by giving up their own privacy.

“TMI can lead to more vulnerability than you want,” said Robin, who noted the distinction between appropriate and inappropriate workplace vulnerability.

Braden Wallake recently laid off two of his 17 employees at HyperSocial, the sales and marketing company he runs. He then went on LinkedIn to post his thoughts. “This will be the most vulnerable thing I’ll ever share,” he wrote.

Wallake, 32, has always tended toward vulnerability, a leadership approach that he attributes to podcaster Joe Rogan. He hosts a weekly “wins call” in which employees talk about triumphs in their professional and their personal lives. He has traveled the country parking his van in some of his employees’ driveways (including, several weeks ago, at the home of one of the workers he had just fired). When he started bawling, moments after laying off two workers, he couldn’t imagine concealing that emotional response. He took a teary selfie for LinkedIn.

“I just want people to see, that not every CEO out there is coldhearted,” Wallake wrote. “I know it isn’t professional to tell my employees that I love them. But from the bottom of my heart, I hope they know how much I do.”

The backlash was swift. The post generated more than 10,000 comments, many noting that Wallake had highlighted his own grief at a moment when his employees were suffering.

“This ‘you don’t know how hard it is for me to fire you all’ vulnerability is something people can stop doing, please,” said Edward Sullivan, an executive coach and co-author of “Leading With Heart.”

Nancy Rothbard, a professor at the Wharton School of the University of Pennsylvania who has studied emotions in the workplace, said her research pointed to a growing expectation that people bring their “full selves” to work, prompted by technologies that blur the lines between work and life. Surveys indicate that people tend to prefer segmenting their professional and personal lives instead of integrating them. But often they don’t feel they have the option.

Julie Brosnan, who works in communications in Washington, D.C., recalled bracing herself for morning meetings with her boss at a previous job, when they would cover topics like: What’d you do last night? What’d you do last weekend? Then the boss would talk about her family fights, her husband and her affair.

Brosnan’s managers referred to the staff as “family.” One worker’s business was everybody’s business. Brosnan was constantly fielding questions about her vacations, children and family life.

“If I was on PTO, everyone would come up to me and be like, ‘Where were you on Friday?’ ” she recalled. “If I was like, ‘I’m going to the dentist,’ they’d be like, ‘What’d you do at the dentist?’ Like, I don’t know!”

It’s a delicate balance. Plenty of executives are relieved that the companies they run don’t have the stifling environments they got accustomed to when starting their careers.

Andy Dunn, for example, who co-founded apparel company Bonobos and now runs Pumpkin Pie, a social app startup, recently gathered his employees on a video call to tell them about his diagnosis of bipolar disorder, which is the subject of a book he released this year, “Burn Rate.”

“Once I got rolling, I kind of overshared,” he said. He got off the call and immediately sent a Slack message to his chief technology officer asking if the conversation had been a “disaster.”

Still, Dunn found that his own vulnerability prompted emotional disclosures from his employees. One person told him that she was feeling lonely in her current stage of life.

“Would she be telling me those things in a different era? I don’t know,” Dunn said, adding that he feels his staff benefits from this openness.

The CEO of dating app Hinge, Justin McLeod, recalled the relief he felt in being completely straightforward with his staff when the company was re-evaluating its business model in 2016, facing stiff competition from Tinder. McLeod laid off half his staff, so he knew he couldn’t protect the rest of the team from confronting the turbulence.

“You can sugarcoat all you want, but it makes people feel less trustful of leadership,” he said.

This summer’s economic tumult has presented a new set of emotional challenges for business leaders. Ariane Goldman, founder of startup Hatch, which sells maternity clothes, has tried to strike a balance between protecting her team from her own anxieties while also being candid about downturns in the market.

“It’s really a positive thing for your team to understand where you’re coming from,” she said. “I’m a founder CEO, not just a corporate gun for hire, so I’m bringing that baggage to the table with me.”

And with the labor market strong, some people are realizing that they can seek out the work environments that make them feel most comfortable, and leave boundary-breaking bosses behind.

Brosnan, for example, now has a group chat with friends who vent their frustrations about boundaries in the workplace. Some feel that their colleagues ask them to disclose too much; others feel strikingly distant from their teammates, especially when interacting with them mostly through video calls. Now Brosnan, who recently started a new job, has finally found a Goldilocks position.

“There’s no expectation that I would need to share pictures of my child or talk about why I’m on PTO,” she said. “We don’t push it, but we’re open and receptive to hearing about it if you’re going through a hard time.”